Even if it is just for this trip, buying a Two Together railcard in the names of the two staff members (cost £30) would save 34% off the £219.40 - I'm assuming that they don't need to leave before 0930 (the railcard is not valid before then).

Second, buying them offpeak returns for Crewe-Wolverhampton, Wolverhampton-Cheltenham, and Cheltenham-Totnes, would reduce £219.40 to £190.20

So my suggestion would cost £190.20 plus £30 for the railcard less approx £64.60 by way of the 34% discount, giving a total of about £155.60 which is a saving of about £64.

[Or for a journey of just over 5 hours (instead of just over 4 hours) leaving on the 1008 on a Monday, an Anytime return via Hereford is £120 with the Two Together discount, i.e. a total of £150 including the cost of the railcard.]

I don't know if Virgin still offer an easement allowing 'peak time' use of Off Peak tickets by charity employees, but, if they do, all travel with that portion of that ticket would need to be on Virgin trains only, as would also be the case for eligible railcard holders (note- this easement does not apply to Two Together railcard holders).

Yes, before 0930 when the fare is set by CrossCountry (XC) is generally not going to be valid on an Off Peak ticket, so you're looking at £229.20 for an Anytime Return (SOR), or an eye-watering price not far short of that for some expensive through Advance fares.

This is because XC want to charge a premium for longer distance passengers at a much higher price than many short distance passengers would pay to occupy the same space.

However you may be interested to learn that a forum member has created a booking engine - Trainsplit - that will sell a combination of tickets at the best price it can find (this is not guaranteed to be the cheapest, though it often will be).

In this case it will sell you tickets at £109.62 (each) if you depart, at 0649 and return at 1850, simply choose your desired times and the site will do the rest.

Alternatively, for £181.80 (i.e. £90.90 per person) the staff members could travel via Hereford on an Anytime Return without any railcard discount. The times of the first three options are (Crewe dep/Totnes arr): 0449/1013, 0555/1117, 0708/1216. But with this ticket they would also have to come back via Hereford. The journey involves changing at Newport (South Wales), and Bristol Temple Meads (except that the penultimate return journey which is on the 1650 involves changing at Taunton instead of Bristol: the last return journey via Hereford involves leaving Totnes at 1850 but there is a tight connection at Newport).